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The band has been active since c. 1984 and was founded as Ashtray Boy and his Country Cousin. During the band's history they have been based in Sydney, Chicago, Vancouver and Melbourne. During the mid-1990s there were two working versions of the band in Sydney and Chicago, with Lee splitting his time between the two cities.

The band is notable for Lee's droll lyrics and singing and odd time signatures. Ashtray Boy has released at nine albums and numerous singles and EPs.

After leaving The Cannanes in 1991 and while continuing Ashtray Boy, Lee also co-fronted Nice (not to be confused with The Nice) with Suzannah Stewart-Lindsay,[1] previously a member of the Adelaide band, Rewind on the Paranoid Side. Francesca Bussey, later to be a member of The Cannanes, was a member of Nice during the recording sessions for their first album but left during production and was credited only as a guest on that release. The group recorded two albums, Nice (1992) and Apple Pie (1993).[1]